WO2005105815A1 - Ionische flüssigkeiten mit fluoralkyltriffluorborat-anionen - Google Patents

Ionische flüssigkeiten mit fluoralkyltriffluorborat-anionen Download PDF

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Publication number
WO2005105815A1
WO2005105815A1 PCT/EP2005/000003 EP2005000003W WO2005105815A1 WO 2005105815 A1 WO2005105815 A1 WO 2005105815A1 EP 2005000003 W EP2005000003 W EP 2005000003W WO 2005105815 A1 WO2005105815 A1 WO 2005105815A1
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pentafluoroethyl
methyl
formula
atoms
alkyl
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PCT/EP2005/000003
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German (de)
English (en)
French (fr)
Inventor
Nikolai Ignatyev (Mykola)
Urs Welz-Biermann
German Bissky
Helge Willner
Andriy Kucheryna
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Merck Patent Gmbh
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Priority to AT05700668T priority Critical patent/ATE517904T1/de
Priority to AU2005238128A priority patent/AU2005238128B2/en
Priority to US10/594,966 priority patent/US8084617B2/en
Priority to JP2007505394A priority patent/JP4960218B2/ja
Priority to EP05700668A priority patent/EP1730157B1/de
Priority to CA002561813A priority patent/CA2561813A1/en
Publication of WO2005105815A1 publication Critical patent/WO2005105815A1/de
Priority to KR1020067020255A priority patent/KR101214027B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the invention relates to ionic liquids with fluoroalklyl trifluoroborate anions, and a process for their preparation.
  • Ionic liquids or liquid salts are ionic species that consist of an organic cation and a generally inorganic anion. They contain no neutral molecules and mostly have melting points below 373 K.
  • ionic liquids e.g. Melting point, thermal and electrochemical stability, viscosity
  • properties of ionic liquids are strongly influenced by the nature of the anion.
  • the polarity and the hydrophilicity or lipophilicity can be varied by the appropriate choice of the cation / anion pair.
  • the object of the present invention was to provide new, thermally and electrochemically and also hydrolysis-stable salt-like compounds to provide low viscosity, which can be used as ionic liquids, as well as a process for their preparation.
  • EP 1 174 941 discloses alkali metal and ammonium salts with fluoroalkyl trifluoroborate anions, in particular lithium or tetraalkylammonium salts, which have high thermal stability and high ionic conductivity and are therefore suitable for use as non-aqueous electrolytes.
  • tetraethylphosphonium trifluoromethyl trifluoroborate is also known from EP 1 229 038. It is also described that heterocyclic cations are also suitable as salts with fluoroalkylborate anions for use as electrolytes without disclosing them in more detail. The present invention is therefore to be regarded as a selection reference to EP 1 229 038. From the article by Zhi-Bin Zhou et al, J. Fluor.
  • Chem 2004, 125, 471-476 are the compounds 1-methyl-3-ethylimidazolium pentafluoroethyl trifluoroborate, 1-methyl-3-ethylimidazolium (n-heptafluoropropyl) trifluoroborate and 1-methyl-3-ethylimidazolium (n-nonafluorobutyl) trif hereby excluded from the scope of protection.
  • the invention therefore relates to compounds of the formula Qi Q2 / [R F BF 3 ] - IX
  • R 1 each independently of one another alkyl having 1-10 C atoms or - (CH 2 ) -R 11 ,
  • R 2 -R 6 is hydrogen or alkyl with 1-10 C atoms
  • R 7 -R 9 is hydrogen, alkyl with 1-10 C atoms or aryl
  • R 10 alkyl with 2-10 C atoms or - (CH 2 ) -R 1 ⁇
  • R 11 perfluorinated or partially fluorinated alkyl with 1-8 C atoms
  • R F means perfluorinated alkyl with 2-8 C atoms and aryl phenyl, fluorinated phenyl or phenyl or fluorinated phenyl substituted by alkyl with 1-8 C atoms.
  • the C C ⁇ o-alkyl group is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, also pentyl, 1-, 2- or 3-methylbutyl, 1, 1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl or decyl.
  • the alkyl groups can optionally be completely or partially fluorinated.
  • cycloalkyl with 3-7 C atoms means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, which may be replaced by F, Cl or Br, in particular F, can be substituted.
  • a group of compounds of the formula I is preferred, XN (R 1 ) 2 and -Q 1 -Q 2 - -CHR 3 -CHR 4 -CHR 5 -CHR 6 , which is represented by the formula Ia
  • R 1 can be represented and wherein the substituents RF, D R1 biirs. D R6 have a meaning given for formula I.
  • R F in formula Ib is preferably pentafluoroethyl, heptafluoropropyl or
  • Nonafluorobutyl particularly preferably pentafluoroethyl.
  • R 1 in formula Ib is preferably CrCio-alkyl.
  • R 2 to R ⁇ in formula Ib is preferably hydrogen or CC 4 alkyl.
  • R F in formula Ic is preferably pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
  • R 1 and R 10 in formula Ic are preferably CrCio-alkyl.
  • the substituents R 7 and R 8 are preferably hydrogen or -CC 4 alkyl. Compounds of the formula Ic in which the substituents R 1 and R 10 are different are particularly preferred.
  • the use of the ionic liquids again preferably being in the foreground as a solvent, extractant or heat transfer agent.
  • the compounds of formula I can be prepared by reacting the corresponding halide of the compounds of formula I with an alkali, alkaline earth metal or ammonium perfluoroalkyl trifluoroborate, prepared by the method of Chambers et al., J. Am. Soc. 82 (1960), 5298 or EP 1 229 038.
  • the invention also relates to a method for producing the
  • R 12 each independently of one another denotes alkyl with 1-8 C atoms, alkoxy with 1-8 C atoms, cycloaikyl with 3-7 C atoms, halogen (F, CI or Br) or aryl,
  • M is ammonium, alkali or alkaline earth metal or a Group 11 or 12 metal
  • R 13 each independently means alkyl having 1-8 C atoms or aryl, and the resulting salt of the formula VM [R F B (OR 13 ) 3 ] V, where M, R F and R 13 is one of the abovementioned Has meanings, is implemented in the second stage with HF
  • R 12 each independently of one another alkyl with 1-8 C atoms, alkoxy with 1-8
  • N-silyl-tris (perfluoroalkyl) phosphazenes used according to the invention can be regarded as a selection in relation to EP 0 250 999.
  • R F is a perfluorinated alkyl having 2 to 4 carbon atoms
  • R 12 is an alkyl having 1-4 C atoms.
  • CF 3 P NSi (CH 3 ) 3
  • CF 3 P NSi (C 4 H 9 ) 3
  • the compound (CF 3 ) 3 P NSi (CH 3 ) 3 .
  • the reaction is advantageously carried out without solvent, temperatures of 10-150 ° C., preferably 50-120 ° C., particularly preferably 60-90 ° C. being suitable.
  • the reaction can also take place in solvents at temperatures between 10 and 150 ° C.
  • Suitable solvents here are benzene, hexane, acetonitrile, dioxane or dimethoxyethane.
  • N-silyl-tris (perfluoroalkyl) phosphinimines are stable liquids, some of which are also air-stable.
  • Perfluoroalkyl here means a perfluoroalkyl group with 1 to 8 carbon atoms. They are great as Perfluoroalkylating. When strong bases are added, perfluoroalkyl anions are released which can react with a wide variety of electrophiles, for example with carbonyl groups.
  • N-silyl-tris (perfluoroalkyl) phosphine imines of the formula II are particularly suitable according to the invention for the production of perfluoroalkyl trifluoroborate anions having 1 to 8 carbon atoms and for the synthesis of compounds of the formula I, as described above.
  • M is ammonium, alkali or alkaline earth metal or a metal of group 11 or 12 and a boric acid ester of the formula IV B (OR 13 ) 3 IV, wherein
  • R 13 each independently means alkyl with 1-8 C atoms or aryl, converted to the salt of the formula VM [R F B (OR 13 ) 3 ] V.
  • Suitable compounds of the formula III are NaF, KF, RbF, CsF, MgF 2 , tetraalkylammonium fluoride, AgF or CdF 2 .
  • KF is particularly preferably used.
  • Suitable boric acid esters of the formula IV are boric acid trimethyl ester, boric acid triethyl ester, boric acid tripropyl ester, boric acid tri (tert-butyl) ester or boric acid triphenyl ester, especially boric acid trimethyl ester.
  • the reaction of the first stage is in an organic solvent
  • Suitable solvents are dimethoxyethane, tetrahydrofuran, diglyme or triglyme. Dimethoxyethane is particularly preferably used.
  • the reaction with HF is preferably carried out in the solvent of the first stage, with the exception of tetrahydrofuran, at temperatures from -10 to 60 ° C., preferably at 0 to 40 ° C., particularly preferably at Room temperature. Without insulation, possibly after previous
  • M is ammonium, alkali or alkaline earth metal or a metal of group 11 or 12, in the third stage with a compound of the formula VII Q 1 Q 2 ⁇ / A- VII ⁇ + where X and -Q 1 -Q 2 - one at Formula I or preferably has the meaning given and
  • This third reaction step can be carried out in water or in a mixture of water and an organic solvent, for example dimethoxyethane, tetrahydrofuran, diglyme or triglyme, or in the pure organic solvent.
  • an organic solvent for example dimethoxyethane, tetrahydrofuran, diglyme or triglyme, or in the pure organic solvent.
  • the third reaction step inevitably gives a mixture of the salts of the formula I according to the invention, as defined above, which also includes the sub-formulas Ia, Ib and Ic, with salts of the formulas VIII, IX and X
  • X, -Q 1 -Q 2 - and R F have the same meaning as for the salts of the formula I or the sub-formulas la, Ib and Ic, forming Villa, Vlllb, Vlllc, IXa, IXb, IXc, Xa, Xb and Xc.
  • the compound of formula II is therefore capable of releasing one, two or all three perfluoroalkyl groups bonded to the P in the reaction.
  • the resulting mixture can contain 50-75 mol% of compounds of the formula I and 25-50 mol% of compounds of the formulas VIII, IX and X.
  • the mixture of the phosphate salts of the formulas VIII, IX and X can consist of 0-75 mol% of the compound of the formula VIII, 0-50 mol% of the compound of the formula IX and 0-25 mol% of the compound of the formula X.
  • the mixture of the salts of the formula I, VIII, IX and / or X is also suitable according to the invention for use as an ionic liquid.
  • the salts can be separated by known methods, in particular by the methods given in the examples.
  • M is ammonium, alkali or alkaline earth metal or a metal from group 11 or 12, can be produced in a targeted manner in a new process, in which respect the substituent R F can also include trifluoromethyl.
  • R F can also include trifluoromethyl.
  • the NMR spectra were measured on solutions in deuterated solvents at 20 ° C. on a Bruker Avance 250 spectrometer.
  • the measuring frequencies of the different cores are: 1 H: 250.13 MHz, 19 F: 235.357 MHz and 31 P: 101.254 MHz.
  • the referencing method is specified separately for each spectrum or for each data set.
  • the phosphates can be prepared from the aqueous by known methods
  • the lower phase is separated from the aqueous phase analogously to Example 2 and washed with small portions of water. It consists of the mixture of the salts N-methyl-N-butylpyrrolidinium pentafluoroethyl trifluoroborate and N-methyl-N-butylpyrrolidinium (pentafluorethyl) pentafluorophosphate and / or N-methyl-N-butylpyrrolidinium bis (pentafluoroethyl) or tetrafluorophosphate and - butylpyrrolidinium hexafluorophosphate.
  • This solid lower phase is taken up in 40 ml of ethanol and 100 ml of water are added, after which N-methyl-N-butylpyrrolidinium pentafluoroethyl trifluoroborate precipitates. This recrystallization is carried out three more times for further purification of the phosphates and the solid is then dried in vacuo at 7 Pa and 50 ° C.
  • N-methyl-N-butylpyrrolidinium (pentafluoroethyl) pentafluorophosphate and the other phosphates can be isolated from the aqueous ethanolic phase by known methods.
  • N-methyl-N-ethylpyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-methyl-N-ethylpyrrolidinium (pentafluoroethyl) pentafluorophosphate and / or N-methyl-N-ethylpyrrolidinium bis (pentafluorethyl) tetrafluorophosphate and / or N-methyl ethyl pyrrolidinium hexafluorophosphate;
  • N-methyl-N-propylpyrrolidinium isolated pentafluoroethyl trifluoroborate or in a mixture with N-methyl-N-propylpyrrolidinium
  • N, N-diethyl-pyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N, N-diethyl-pyrrolidinium (pentafluoroethyl) pentafluorophosphate and / or N, N-diethyl-pyrrolidinium bis (pentafluorethyl) tetrafluorophosphate and / or N, N-diethyl pyrrolidinium hexafluorophosphate;
  • N N, N-dibutyl-pyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N, N-dibutyl-pyrrolidinium (pentafluorethyl) pentafluorophosphate and / or N, N-dibutyl-pyrrolidinium bis (pentafluoroethyl) tetrafluorophosphate and / or pyrrolidinium hexafluorophosphate;
  • N, N-dioctyl-pyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N, N-dioctyl-pyrrolidinium (pentafluoroethyl) pentafluorophosphate and / or N, N-dioctyl-pyrrolidinium bis (pentafluoroethyl) tetrafluorophosphate and / or pyrrolidinium hexafluorophosphate;
  • N, N-dinonyl-pyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N, N-dinonyl-pyrrolidinium (pentafluoroethyl) pentafluorophosphate and / or N, N-dinonyl-pyrrolidinium bis (pentafluoroethyl) tetrafluorophosphate and / or N, N- pyrrolidinium hexafluorophosphate;
  • N, N-didecyl-pyrrolidinium pentafluoroethyl trifluoroborate isolated or in a mixture with N, N-didecyl-pyrrolidinium (pentafluoroethyl) pentafluorophosphate and / or N, N-didecyl-pyrrolidinium bis (pentafluorethyl) tetrafluorophosphate and / or N, N- pyrrolidinium hexafluorophosphate.
  • the lower phase with the mixture of the salts N-butylpyridinium pentafluoroethyl trifluoroborate and N-butylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-butylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-butylpyridinium hexafluorophosphate is separated from the aqueous phase 70 and malafluorophosphate with 10 malafluorophosphate Washed water. After the water has been distilled off, the oily residue is washed again with water and the phosphates are thus separated off.
  • N-butylpyridinium (pentafluoroethyl) pentafluorophosphate and the other phosphates can be isolated from the aqueous phase by known methods.
  • N-methylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-methylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-methylpyridinium bis (pentaf! Uorethyl) tetrafluorophosphate and / or N-methylpyridine hexafluorophosphate;
  • N-ethylpyridinium pentafluoroethyl trifluoroborate or in a mixture with N-ethylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-ethylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-ethylpyridinium hexafluorophosphate;
  • N-propylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-propylpyridinium (pentafluorethyl) pentafluorophosphate and / or N- Propyl pyridinium bis (pentafluoroethyl) tetrafluorophosphate and / or N-propyl pyridinium hexafluorophosphate;
  • N-Pentylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-Pentylpyridinium (pentafluorethyl) pentafluorophosphate and / or N-
  • N-hexylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-hexylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-
  • N-heptylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-heptylpyridinium (pentafluorethyl) pentafluorophosphate and / or N-heptylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-heptylpyridinium; hexafluorophosphate;
  • N-octylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-octylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-octylpyridinium bis (pentafluoroethyl) tetrafluorophosphate and / or N-octylpyridinium hexafluorophosphate;
  • N-nonylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-nonylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N-nonylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-nonylpyridinium hexafluorophosphate;
  • N-decylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-decylpyridinium (pentafluorethyl) pentafluorophosphate and / or N-decylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-decylpyridinium hexafluorophosphate;
  • N- (i-propyl) -3-methylpyridinium pentafluoroethyl trifluoroborate isolated or mixed with N- (i-propyl) -3-methylpyridinium (pentafluoroethyl) pentafluorophosphate and / or N- (i-propyl) -3-methylpyridinium bis ( pentafluoroethyl) tetrafluorophosphate and / or N- (i-propyl) -3-methylpyridinium hexafluorophosphate;
  • N-propyl-3-methylpyridinium pentafluoroethyl trifluoroborate isolated or in a mixture with N-propyl-3-methylpyridinium (pentafluorethyl) pentafluorophosphate and / or N-propyl-3-methylpyridinium bis (pentafluorethyl) tetrafluorophosphate and / or N-propyl-propyl methyl pyridinium hexafluorophosphate;
  • Viscosity data are listed in Table 1 below. The viscosity was determined using a SVM3000 viscometer from Anton Paar, Austria, the standard procedure being carried out as described in the accompanying material for the viscometer.
  • Scan rate 20 mV / S N-butyl-N-methylpyrrolidinium (pentafluoroethyl) trifluoroborate is dissolved 0.5 molar in acetonitrile and the solution is measured in a glove box under argon at room temperature.
  • the cyclic voltamogram in FIG. 1 shows that the compound has a high electrochemical stability in the range from -3 to +4 V (zero is referenced for E ° by ferrocene).
  • Example 7 Thermal stability The following table 2 lists the rate at which the perfluoroalkylborate compound is decomposed into tetrafluoroborate compounds. These data clearly show that trifluoromethyl trifluoroborate salts are not thermally stable.
  • the decomposition rate was determined by heating the samples to 150 ° C. and measuring them by 19 F NMR spectroscopy.
  • the extract is washed with 0.1 M hydrochloric acid and water and dried over MgSO 4.
  • the solvent diethyl ether is distilled off and the residue is fractionally distilled, the fraction at 110-115 ° C. corresponding to the compound 2,2,3,3,3-pentafluoro-1-phenylpropan-1-ol (2.3 g).
  • the yield is 63.2%.

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PCT/EP2005/000003 2004-04-02 2005-01-03 Ionische flüssigkeiten mit fluoralkyltriffluorborat-anionen WO2005105815A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AT05700668T ATE517904T1 (de) 2004-04-02 2005-01-03 Ionische flüssigkeiten mit fluoralkyltriffluorborat-anionen
AU2005238128A AU2005238128B2 (en) 2004-04-02 2005-01-03 Ionic liquids comprising fluoralkyltriffluoroborate anions
US10/594,966 US8084617B2 (en) 2004-04-02 2005-01-03 Ionic liquids having fluoroalkyltrifluoroborate anions
JP2007505394A JP4960218B2 (ja) 2004-04-02 2005-01-03 フルオロアルキルトリフルオロボレートアニオンを有するイオン液体
EP05700668A EP1730157B1 (de) 2004-04-02 2005-01-03 Ionische flüssigkeiten mit fluoralkyltriffluorborat-anionen
CA002561813A CA2561813A1 (en) 2004-04-02 2005-01-03 Ionic liquids having fluoroalkyltriffluoroborate anions
KR1020067020255A KR101214027B1 (ko) 2004-04-02 2006-09-28 플루오로알킬트리플루오로보레이트 음이온을 포함한 이온성액체

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DE102004017026.6 2004-04-02
DE102004017026A DE102004017026A1 (de) 2004-04-02 2004-04-02 Ionische Flüssigkeiten mit Fluoralkyltrifluorborat-Anionen

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AT (1) ATE517904T1 (ja)
AU (1) AU2005238128B2 (ja)
CA (1) CA2561813A1 (ja)
DE (1) DE102004017026A1 (ja)
ES (1) ES2368924T3 (ja)
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JP2010502754A (ja) * 2006-09-12 2010-01-28 ズルツァー・ケムテック・アーゲー イオン性液体の精製方法
KR20140066724A (ko) * 2011-08-24 2014-06-02 바스프 에스이 전기화학 또는 광전자 소자용 황-함유 첨가제
DE102014016583A1 (de) 2014-11-11 2016-05-12 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Perfluoralkylfluoroboratsalzen
DE102016009846A1 (de) 2016-08-16 2018-02-22 Julius-Maximilians-Universität Würzburg Fluoralkylhydrido- und Fluoralkylcyanohydridoborate
EP3456725A1 (en) * 2017-09-13 2019-03-20 Freie Universität Berlin Pentafluorophosphate derivative, its uses and an appropriate manufacturing method

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WO2011031401A2 (en) * 2009-08-28 2011-03-17 Brookhaven Science Associates Llc Lithium non-fluorinated and fluorinated phenyl trifluoro borate salts for non-aqueous battery electrolytes
US9079156B2 (en) 2010-06-29 2015-07-14 Reliance Industries Ltd. Ionic fluids
CN109438511B (zh) * 2018-12-11 2020-11-06 河南省科学院化学研究所有限公司 一种合成四氟硼酸二叔丁基苯基膦鎓盐的方法
KR102648804B1 (ko) * 2021-12-09 2024-03-15 부산대학교 산학협력단 마이크로웨이브 또는 연속 흐름 반응 공정을 이용한 이온성 액체의 합성방법
CN114720541B (zh) * 2022-05-07 2023-10-27 中国标准化研究院 一种提高红花椒麻感强度分级准确性的方法

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JP2014529601A (ja) * 2011-08-24 2014-11-13 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 電気化学または光電子デバイスのための硫黄含有添加剤
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TW200613270A (en) 2006-05-01
EP1730157A1 (de) 2006-12-13
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